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通过连续的铜催化C-N偶联/环化和氧化反应合成N-稠合苯并咪唑-4,7-二酮

Synthesis of N-Fused Benzimidazole-4,7-diones via Sequential Copper-Catalyzed C-N Coupling/Cyclization and Oxidation.

作者信息

Dao Pham Duy Quang, Ho Son Long, Cho Chan Sik

机构信息

Department of Applied Chemistry, Kyungpook National University, 80 Daehakro, Bukgu, Daegu 41566, Republic of Korea.

出版信息

ACS Omega. 2018 May 25;3(5):5643-5653. doi: 10.1021/acsomega.8b00805. eCollection 2018 May 31.

DOI:10.1021/acsomega.8b00805
PMID:31458764
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6642034/
Abstract

2-(2-Bromovinyl)- and 2-(2-bromoaryl)-benzimidazoles, including their 4,7-dimethoxy analogs, react with primary amides by microwave irradiation (or usual heating) in dimethylformamide in the presence of a catalytic amount of CuI along with a base to give the corresponding benzo[4,5]imidazo[1,2-]-pyrimidines and -quinazolines in good yields. Treatment of benzo[4,5]imidazo[1,2-]-pyrimidines and -quinazolines having methoxy group on benzimidazole moiety with aqueous ceric ammonium nitrate affords unprecedented N-fused hybrid scaffolds, benzo[4,5]imidazo[1,2-]-pyrimidin-6,9-diones and -quinazoline-8,11-diones, respectively, in high yields.

摘要

2-(2-溴乙烯基)-和2-(2-溴芳基)-苯并咪唑，包括它们的4,7-二甲氧基类似物，在催化量的碘化亚铜和碱存在下，于二甲基甲酰胺中通过微波辐射（或常规加热）与伯酰胺反应，以良好的产率得到相应的苯并[4,5]咪唑并[1,2-]嘧啶和喹唑啉。用硝酸铈铵水溶液处理苯并咪唑部分带有甲氧基的苯并[4,5]咪唑并[1,2-]嘧啶和喹唑啉，分别以高收率得到前所未有的N-稠合杂化骨架，即苯并[4,5]咪唑并[1,2-]嘧啶-6,9-二酮和喹唑啉-8,11-二酮。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7695/6642034/fc45ec2a951e/ao-2018-00805z_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7695/6642034/d73743dd1290/ao-2018-00805z_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7695/6642034/fc45ec2a951e/ao-2018-00805z_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7695/6642034/d73743dd1290/ao-2018-00805z_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7695/6642034/fc45ec2a951e/ao-2018-00805z_0004.jpg

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本文引用的文献

1
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2
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J Org Chem. 2017 Jan 6;82(1):331-342. doi: 10.1021/acs.joc.6b02423. Epub 2016 Dec 12.
3
Microwave-assisted green construction of imidazole-fused hybrid scaffolds using 2-aminobenzimidazoles as building blocks.
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RSC Adv. 2021 Jun 17;11(35):21367-21374. doi: 10.1039/d1ra04396j. eCollection 2021 Jun 15.
4
Weak Base-Promoted Lactamization under Microwave Irradiation: Synthesis of Quinolin-2(1)-ones and Phenanthridin-6(5)-ones.微波辐射下弱碱促进的内酰胺化反应：喹啉-2(1)-酮和菲啶-6(5)-酮的合成
ACS Omega. 2018 Sep 27;3(9):12114-12121. doi: 10.1021/acsomega.8b01742. eCollection 2018 Sep 30.
5
Synthesis of Pyrimidine- and Quinazoline-Fused Benzimidazole-4,7-diones Using Combinatorial Cyclocondensation and Oxidation.利用组合环化缩合和氧化反应合成嘧啶并喹唑啉稠合的苯并咪唑-4,7-二酮
ACS Omega. 2018 Dec 17;3(12):17456-17465. doi: 10.1021/acsomega.8b02755. eCollection 2018 Dec 31.
Rh-Catalyzed Reactions of 1,4-Benzoquinones with Electrophiles: C-H Iodination, Bromination, and Phenylselenation.
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4
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J Med Chem. 2016 Jun 9;59(11):5209-20. doi: 10.1021/acs.jmedchem.5b01571. Epub 2016 May 26.
5
Copper-catalyzed tandem Ullmann type C-N coupling and dehydrative cyclization: synthesis of imidazo[1,2-c]quinazolines.铜催化串联乌尔曼型C-N偶联和脱水环化反应：咪唑并[1,2-c]喹唑啉的合成
Org Biomol Chem. 2016 Feb 7;14(5):1736-41. doi: 10.1039/c5ob02469b.
6
Synthesis of novel azole-fused quinazolines via one-pot, sequential Ullmann-type coupling and intramolecular dehydrogenative C-N bonding.通过一锅法、连续的乌尔曼型偶联和分子内脱氢C-N键合合成新型唑并喹唑啉类化合物。
Org Biomol Chem. 2015 Mar 14;13(10):2947-50. doi: 10.1039/c4ob02375g.
7
Copper-catalyzed C-H functionalization reactions: efficient synthesis of heterocycles.铜催化的C-H官能团化反应：杂环的高效合成
Chem Rev. 2015 Feb 11;115(3):1622-51. doi: 10.1021/cr500410y. Epub 2014 Dec 22.
8
Synthesis and biological evaluation of benzo[4,5]imidazo[1,2-c]pyrimidine and benzo[4,5]imidazo[1,2-a]pyrazine derivatives as anaplastic lymphoma kinase inhibitors.苯并[4,5]咪唑并[1,2-c]嘧啶和苯并[4,5]咪唑并[1,2-a]吡嗪衍生物作为间变性淋巴瘤激酶抑制剂的合成及生物学评价
Bioorg Med Chem. 2014 Feb 15;22(4):1303-12. doi: 10.1016/j.bmc.2014.01.007. Epub 2014 Jan 10.
9
Decarboxylative cross-coupling of mesylates catalyzed by copper/palladium systems with customized imidazolyl phosphine ligands.
Angew Chem Int Ed Engl. 2013 Mar 4;52(10):2954-8. doi: 10.1002/anie.201208025. Epub 2013 Feb 5.
10
Copper-catalyzed sequential Ullmann N-arylation and aerobic oxidative C-H amination: a convenient route to indolo[1,2-c]quinazoline derivatives.铜催化的串联 Ullmann N-芳基化和有氧氧化 C-H 胺化：一种方便的吲哚并[1,2-c]喹唑啉衍生物合成途径。
Org Lett. 2012 Aug 3;14(15):3894-7. doi: 10.1021/ol3016435. Epub 2012 Jul 13.